75318-45-5Relevant articles and documents
Synthesis and Reactions of 4,5-Dichloro-1,2,3-dithiazolium Chloride
Appel, Rolf,Janssen, Heinrich,Siray, Mustafa,Knoch, Falk
, p. 1632 - 1643 (2007/10/02)
Disulfur dichloride reacts with acetonitrile via chloro- and dichloroacetonitrile to give finally 4,5-dichloro-1,2,3-dithiazolium chloride (1).The reactivity of 1 with proton-active compounds is determined by the nucleophilic substitution of the chlorine at carbon atom C-5.Substrates like H2O, H2S, primary amines, and sulfonamides, having two active hydrogen atoms, form the covalent 4-chloro-5H-1,2,3-dithiazole derivatives 2, 3, 5. 1 reacts with phenols in o- or p-position by an electrophilic attack to form 4-chloro-5-(hydroxyphenyl)-1,2,3-dithiazolium chlorides 9a - d.HCl elimination from these leads to deep violet, metallic-reflecting crystals of the betaine-like neutral molecules 10a, b.X-ray analysis shows a planar structure of 10a and a molecular arrangement of a right and a left helix.Ring cleavage of 1 with chlorine gives compounds 14, 15; correspondingly, 2 reacts with chlorine to yield 2-chloro-2-(chlorothioimino)acetyl chloride (18).
